The Cheat Sheet You're Not Using

I give every person going on an introduction through Wayward Hearts a match document.

While it only takes people a few minutes to read it, it actually takes me a couple of hours to prepare it.

It has a bio of the person they are about to meet, which is pretty standard for any type of dating app or matchmaker. But the rest of document is where you are really getting value for your membership.

The second section explains exactly what I see in this match. The values you share with each other; the common ground, the reason why as a matchmaker I am putting these two people in the same room.

And then a third section devoted to what these two people have in common.

This section is a Gold Mine! But it seems like PEI is lacking in gold miners…..

I know this section is a gold mine because I wrote it. I know what is in it. I have deliberately thought through every detail and sentence written in it so it gives you the best information to start a conversation that will allow you to actually get to know each other. It contains facts about what your shared interests actually are. You don’t have to guess. You have them in front of you in black and white. It’s your job to use them.

And I know, from the feedback I receive after dates, which people have read it carefully and which people speed read through it, forget about what I wrote, and walk in cold to the introduction. Then act like you have nothing in common, which I know is factually untrue because I have specifically matched you togeather because you have something in common.

Here is what I want to say to the second group.

This is not rocket science, people.

I cannot sit across that table with you. I cannot whisper in your ear when the conversation stalls. I cannot remind you that you both love hiking the Confederation Trail, that you both love going to live concerts, that you both left careers you were good at to do something that actually mattered to you.

That information is sitting right there in the document I sent you. It is a conversation waiting to happen. All you have to do is use it.

Before your next introduction, read the shared interests section and ask yourself two questions. What could I ask them about this? And what could I share about myself that connects to it?

That is it. That is the whole strategy.

A good first date conversation is not about being witty or charming or having the perfect opening line. It is about being curious enough to ask and present enough to listen. And then -- this part matters -- letting them know something real about you in return.

Nobody wants to go on a second date with someone who treated the whole thing like a job interview. Ask questions, yes. But answer them too. Show up as a person, not an audition panel.

The match document gives you the tools. The conversation is yours to have.

Use the cheat sheet.

waywardhearts.ca 💙

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ONE YEAR OF WAYWARD HEARTS: WHAT I PLANNED AND WHAT ISLANDERS TAUGHT ME